When did that happen
by madd09
Summary: A fun two shot about the cast wondering when did Blair and Dan get so close


A/N so this is part 1 of 2 it's just a fluffy Dair piece so some of the characters might be oc. I know the grammar is probably horrible if you are willing to beta let me :)

3 Madd09

"We're going to be late to my mother's Brunch Humphrey."

"I don't even remember being invited Waldorf. And we're in a taxi it's not like I control the traffic."

" If you had have been more cooperative we wouldn't be running late."

"Where here Humphrey chop chop."

" You know you're more than just an evil dictator of taste you're an evil dictator period."

"Thank you. I can't wait for everyone to see your hair it looks so much better."

"I still can't believe actually I can it is something you would do but I didn't think you would go to such extremes."

"Well you obviously undermested me didn't you."

"Miss Blair your home and you have Mr Dan with you good everyone one is here now. Everyone else is waiting for the two of you in the dining room."

"Let's go Humphrey people to impress."

"Dan you finally got your hair cut it looks good." Exclaimed Lily

"See Humphrey even Lily thinks it looks good."

"I never said it didn't look good Waldorf I just liked my hair the way it was."

"Extreme time call for extreme measures. Don't be mad"

" Extreme measure, you stole my keys and got a set cut for you. Then you snuck into my apartment at 5:00 am. Snuck into my bedroom and proceeded to randomly chop my hair. I woke up with you leaning over me holding a pair of scissors and grinning like a mad man.  
>You then proceeded to yell at me to get dressed. Then you threatened to cut Cedric's head off if I didn't make you waffles. After breakfast you dragged me to a hair salon to fix my hair that you ruined. Then you complained on the way here that we were going to be late and that it was my fault so yes Blair I'm mad.<p>

"Well you have no reason to be Humphrey if I'm going to be your date tonight you need to look acceptable."

"That's another thing you invited yourself."

"Humphrey you should be honoured that I'm accompying you tonight."

"I wouldn't mind if you weren't a manipulative bitch who forced me to get a haircut and won't let me wear what I want."

"Blair Dan please sit down so we can start brunch." Scolded Eleanor

"Sorry."  
>Sorry."<p>

"So we're the two of you going tonight." inquired Serena.

"A dinner with some of the best writers in the world Humphrey was one of the up and comers invited it's a great honour." Blair answered

"Oh sound like fun." Serena replied sarcastically.

"It will be, there will be some of the best writers of today that we get to talk to. We can ask them their opinions on classics." gushed Blair Serena just looked at her disbelieving which was the look everyone else seemed to be spotting.

The rest of Brunch was a lot less lively until that is Blair looked at her phone and realized that her and Humphrey had to leave right then if they we're going to be ready in time seeing as they still had to buy something for him to wear.

Chuck was the first to speak after their abrupt departure. "When the hell did that happen?"

"What was that?" replied Nate. "Are they friends."

That was a question that no one had an answer to. Eleanor decided to question Doretta as even the adults were curious about the development.

"It happened over Christmas break they were the only 2 left in the city. They ended up running into each other at the movies apparently. Then it happened again than Miss Blair said the started planning it to happen. Then Mr Dan was meeting Miss Blair here for lunch or Miss Blair was going to Brooklyn to see Mr Dan then they started having Movie nights. Miss Blair says there friends."

"Thanks Doretta."

"I dot get it I tried to get the two of them to be friends for years they hated each other." exclaimed Serena. " you're telling me all it took was them being the only two left in the city to find out how much they have in common and to become friends"

"Anyone else finding it difficult to wrap their head around Blair voulanteraly going to Brooklyn?" Asked Nate  
>There was a unanimous yes by the room occupants before everyone got lost in thought.<p>

Chuck was the first to snap out of with an evil smirk appearing on his face." Well there is only one way to get to the bottom of this." when faced with the blank looks he went on. "We have to stalk them."  
>Rufus was the first to reply. "I don't think that's a good idea."<p>

Serena agreed whole heartedly with Chuck though. "It's a perfect idea Rufus and you Eleanor and Mom have to help."

"Why exactly do we have to help." inquired Lily.

"Because mom you are all just as curious about this as the rest of us and we need you to talk to Blair and Dan."

Eleanor replied sceptically. "Why exactly do you need our help?"

"Isn't it obvious." replied Nate in a how stupid are you tone. "I and Chuck can't exactly ask Dan. Hey buddy what are you up to with our ex-girlfriend. Any more than Serena can ask Blair what she's up to with her ex-boyfriend. It would just be weird but as their parents you don't have that problem."

"So let me get this right you want me to ask my Son what exactly Chuck."

" You and Eleanor just need to ask them about each other and report back to us."

"I would like to know why my daughter is suddenly voluntarily spending time in a place she has always refused and hated to go to. It doesn't make sense."

Nate then piped up with the question no one else had the guts to ask. "What if there falling for each other."

Serena burst into laughter when she calmed down she made it quite clear what she thought about that. "Guys this is Blair Waldorf were talking about it no way would she fall for someone from Brooklyn, someone with no money."

" Serena he may be Brooklyn but he's now a bestselling author he went to the same school and college as Blair he gets invited to our party's he may not have the money but he is an UES now." Nate tried to explain.

"Ok look whether or not there is something more or not is what we have to find out. Rufus, Lily your job is to find out from Dan what he thinks of Blair. Eleanor your Job is the opposite. Serena you need to plan a girl's night just you and Blair see if she brings Humphrey up in conversation. Me and Nate will do the same thing. Everyone send a group text with progress." ordered Chuck.

Blair  
>Hey B make sure you text us a photo of you and Dan all dressed up tonight.<br>Serena  
>Serena<br>I will the suit I've picked out for him looks amazing and he actually found this tie that matches my dress perfectly. The night is going to be amazing. We're watching breakfast at Tiffany's before we have to get ready. Dan's just going to crash at mine tonight so don't be surprised if you see him in our bathroom.  
>Blair<br>Blair  
>is he staying in your room?<br>Serena  
>Serena<br>Yeah we should be home around 11 and were going to finish the night by having an Audrey Hepburn marathon. I gtg 3  
>Blair<br>Chuck; Eleanor; Lily; Nate; Rufus  
>so guess who is crashing in Blair's bed tonight.<br>Serena  
>Chuck; Eleanor; Nate; Rufus; Serena<br>so that just means there friends the four of you have shared a bed countless times.  
>Lily<br>Chuck; Lily; Nate; Rufus; Serena  
>Would you all like to do brunch again tomorrow so you kids can question them when they awake.<br>Eleanor  
>Of course the reply was a unanimous yes<br>meanwhile at the loft

"Blair I don't have a maid here you have to clean up after you're finished in the bathroom and not leave your makeup everywhere."

"Maybe you should hire a maid then Humphrey."

"Blair I don't need one I live by myself it's you I'm always picking up for anyway."

" Stop delaying the in edible Humphrey and get out here I got ready quicker."

"Wow I'm good you actually look hot Humphrey. Come here Serena want as a photo of the 2 of us. "

At the dinner  
>"Dan Humphrey right? Scott smith."<p>

"Yea and I love your work. This is Blair Waldorf my friends."

"Humphrey I'm your best friend you would be lost without me and would continue to scare people with your fashion choices. He also based Claire on me."  
>"Sorry best friend and yes Claire was inspired by you."<p>

the next morning.  
>Doretta had been given strict instructions to not wake Blair or Dan or to even go into her room. Once everyone was there Serena, Nate and Chuck. Snuck into Blair's room to find Dan laying on his back with Blair practically curled up on top of him blankets kicked down to the end of the bed. With the TV showing the title screen of the movie the fell asleep watching. All in all it was adorable. So in other words the three schemers were all standing in the doorway with their jaws dropped. After a couple of minutes the adults come up to see why there was no movement. They were all shocked as well but unlike the kids snapped out of it. Eleanor strode forward to wake the pair up. This snapped the others out of their shock.<p>

"Blair time to get up. Lily Rufus chuck Nate and Serena are here to have brunch with us."

"We had brunch yesterday me comfy go away." an proceeded to snuggle in closer to Dan.

" Let me try Eleanor."

"Dan wake up were having brunch at Blair's again I brought a box of photos from when you were a kid."

That worked Dan sat up abruptly and because of the position they ended up with him leaning against the headboard with Blair still asleep curled up in his lap with her head on his chest and an hand fisted in his shirt.

"Don't worry son I just said that to wake you up Blair refuses to get up."  
>Dan looked at the clock and saw that thy hadn't been asleep long a Blair hadn't drifted off till a little after sunrise with him following not long after.<br>"Don't worry Dad I'll wake her up." Dan then proceeded to pick her up and slowly got off the bed cradling Blair bridal style and slowly walked towards the bathroom where he opened though then he placed her on the floor of the shower and turned the water on to freezing cold. It was only a matter of seconds until Blair started screaming which caused Dan to start laughing. Blair took one look at Dan standing there laughing before she stood up screaming "Humphrey I'm going to get you" and started chasing him. They were followed by Nate who had started videoing the minute Dan said he would wake her and found the whole thing hilarious Dan laughing like a mad man and Blair drenched and out for blood.

Unfortunately for Dan, Blair had the advantage of it being her home. It was as they were coming thru the sitting room for the 3rd time were everyone else sitting watching the morning entertainment that Dan made a mistake he turned around to see where Blair was. When he turned back around he was about to run into a stool so he had to slow down to make it round and that was all Blair needed. She's saw her chance and it took she jumped an tackled Dan to the floor where she started punching him. Dan grabbed both of her wrists so she would stop punching but that just started the yelling. It seemed like it was never going to stop until that is Blair so Chuck out of the corner of her eye. She froze and then started to slowly look around. Embarrassed she started. "Well I guess I should go Finnish my shower, Humphrey I'll show you which one to use let's go." and proceeded to hightail it out of there.

"I want a copy of that video Nate." Serena managed to get out amidst her giggles.

"Sure maybe there will be a clue in it that Blair is being possessed" suggested Chuck.  
>They spent the next ten minutes till Dan appeared debating whether or not Blair was possessed. Once he arrived Lily started to ask Dan about last night before anyone could ask him about Blair.<br>After another ten minutes Blair appeared.  
>"So why are we hosting brunch again mother."<p>

"Were all so busy with our lives now Blair we rarely get to all meet together and everyone had a free day so we figured we would spend it together catching up."

"All day Mother."

"All day Blair, I know you don't have plans now let's all reconvene in the dining room for some food."

Blair was the last to walk in to the room." Humphrey what are you doing." she demanded.

"Siting down to eat like your mother told us to." he replied like it was the most obvious thing in the world which it was after Blair was finished rolling her eyes and staring at him like he had just suggested she wear something from last season she replied. "I meant why are you sitting down there Humphrey my seats up here."

"I wasn't aware that I had to sit next to you Waldorf."

"Have you ever had a best friend before Humphrey? You have to sit next to me so I can dump the food I don't like on your plate and steel thee food I do like off your plate."

"I have had a best friend before Waldorf and I'm pretty sure there is meant to be an equal amount of give and take from both parts. Now if you want to steel my food there is an empty chair next me."

Blair knew he wasn't going to give in so she stomped over to the seat he was indicating. We're Dan was already piling food onto her plate.

"So Blair did you enjoy your thing with Dan last night."

"Yeah it was really interesting It  
>was glad to get their opinions and to be able to debate over our favourite books, wasn't it Humphrey"<p>

"Hmm whatever you say my evil dictator or taste."  
>Replied Dan too busy enjoying the food to pay any real attention<p>

"Ah so you're the one that came up with that for Blair." exclaimed Eleanor.

"Yeah whatever were talking about or doing it always comes back to my clothes or hair."

"Your hair is fine now I fixed it Humphrey." Blair told him running her fingers through his hair." and so is your wardrobe now that I threw all your plaid at a homeless guy yesterday while you were in the shower."

Dan went about 100 different shades in the next couple of seconds. Everyone was holding their breath waiting for him to explode. Except Blair who just looked amused. Dan swallowed and then opened his mouth the closed it again.

"It's no different when you threw out my headbands when we're in collage."

"That was fun it felt good to. I guess I can forgive you."

" Good because that's what we should do today. We should all go to Humphrey's and go through his closest. Then with the lovely fat check you got we can buy you a new wardrobe I might allow 1 piece if plaid if your good.

"I don't need a new wardrobe Blair."

"Let's ask our friends Serena?"

"Yes."

"Chuck?"

"Yes."

"Nate?"

"Yes."

"Mother?"

"Yes."

"Lily?"

"Yes."

"Rufus?"  
>One look at Lily and his answer was<br>"Yes."  
>"See Humphrey our friends and family agree."<br>"You've turned my farther into a traitor Lily. I can't believe you took Blair side you're meant to be my farther."

"You know Dan you brought this upon yourself you refer to her as your evil dictator of taste so she is just fulfilling the requirement." joked Serena  
>Dan was about to reply when his phone went off.<p>

"Hello who is this."?  
>"It's Vanessa Dan where are you?"<br>" I'm having brunch at Blair's with her Eleanor, dad, lily chuck, Serena and Nate. Who after lunch are all apparently going through my wardrobe"

"Let me guess it way your new beast friend's idea."

"Yeah it was Blair's idea."

"You're always with her Dan your letting her go through your closet remember when you hated her hated the UES she's a manipulative bitch of a princess I don't understand."

"You're right Blair is a manipulative bitch of a princess at first glance. But then you get to know her and she is smart she really works for what she wants. She's loyal until you give her a reason not to be. Once you really get to know her you learn that she idolizes Audrey Hepburn that she loves curling up watching her movies and gorging on snacks. But the thing I like most about her Vanessa is that no matter whether we are enemies' frenemies friends or best friends whenever something happens she ask for my version she hears me out. Blair Waldorf is a 100x better person than you ever have been and can ever hope to be."  
>He hung up with those parting words the next he knew he had a 95 pound doe eyed brunette crying into his shoulder.<br>"Do you really mean all that Dan?" Blair managed to get out through tears.

"Of course I did Blair every word I wouldn't have said them I didn't mean It." he looked around the room and saw everyone had finished. "how but we go over to the loft now so you can destroy my wardrobe sweetheart."  
>She just nodded her head in response. Still clinging to him.<p>

"We will meet you guys there." Lily suggested and ushered everyone out to give the two of them some privacy.

Luckily having access to a town car they all could fit in the one car. Rufus was the first to speak.  
>" if you had of told me a year ago or even a month ago that not only would Dan defend Blair to Vanessa but that he would do it the way he did I would have called you crazy and suggested you seek help."<br>"We have to get them together."  
>"Chuck are you possessed to now."<br>"No I'm not possessed Nate but those were happy tears up there. This morning she was having fun he brings out the real Blair everyone in here loves her don't we want that for her.

"Chucks right Nate." said Serena  
>"Alright so how are we going to do this." Nate replied.<p>

Everyone pondered that Lily was the first to speak. "We will watch them while we're going through Dan's wardrobe. Then come up with a plan we can implement  
>while we're shopping. Which we will use during dinner."<p>

Everyone agreed that that sounded like a good idea as any. Due to the fact the left first they got to the loft and were able to take on all the surroundings noticing that A few things spread out around the loft belonged to Blair. Like the copy of Vogue on the coffee table which definitely wasn't Dan's.

Of course while Dan and Blair were friends now they hadn't really changed and the group could hear them before they saw them arguing about some exhibition they had gone to.

The argument was over the second they were through the door Blair was all about finally fixing Dan's wardrobe.  
>"So this how this is going to work. You each need to find a place to sit in Dan's room. I'll give you all a plastic bag. Except mom you need to write a list of what we need. I'll pick the items out of Dan's cupboard and ask for a vote on whether or not to chuck it. Dan you can have 10 saves, everyone else has 2. Everyone got it. Good let's get started."<p>

That's how the next two hours were spent with Blair holding an item up, getting a vote, then Dan saving or tossing. And Eleanor writing down what they needed to get. In the end they got rid of most of the things from high school Dan and the articles of clothing that were worn out.

They decided to hit lunch before the shopping or more like the males wined until the females agreed. They decided they would take a taxi to one of Chuck's favourite restaurant they ended up having to take three cabs. One for the three schemers, one for the parents and one for the duo.

Of course the fact that Blair an Dan had their own cab was purely coincidental. It was also just a weird chance that Serena happened to call Lily and that both phones were placed on speaker.

"There all up to something aren't they." asked Dan.  
>"Yep, why else would we all be sending the day together they are probably trying to figure us out."<p>

"Were best friends what's there to figure out?"

"They probably think we're either something more or should be something more."

"So what's the plan Blair?"

"What makes you think I have a plan Dan?"

"You mean besides the fact that you're Blair Waldorf."

"True, okay so knowing them as I do it will be Nate, Chuck and Serena as the main schemers. But they had to bring our parents seeing as Serena can't ask me If I like her ex. same with the boys and you so that will be our parents job."

"Okay so what do I have to do."

"When I'm not around just start talking about something we've done always try and bring the conversation back to us. I'll do the same thing."

"Okay so do you want then to relieve that we like each other or that we are together."

"At the moment just that we like each other so basically just follow my lead like usual."

"Ha ha that never gets old Blair. Are you ready to manipulate our friends and family."?

"I'm always ready Dan."

They shared a smile before getting out of the cab. Where Blair proceeded to grab hold of Dan's hair as the headed inside the restaurant.

Blair and Dan made their way across the restaurant to we're the rest of their part was seated. Just as they were seated a waiter turned up asking for drinks and entrees.

"What's good?" asked Dan.  
>"It's all good Dan." Replied Blair.<br>"Might I suggest sir you and your girlfriend get the couple special? You get a bit of everything of the entree's to share. Then your own main meal each. Followed by an ice cream sundae to share. "Suggested the waiter.

"That sounds great to me. Blair?"  
>"It sounds delicious well take that."<br>"Blair, mom, Eleanor. Come with me to powder my nose." Serena more demanded than asked as she already was yanking Blair out of her seat before shed even finished her sentence.

Once they got to the bathroom and Serena has checked that it was empty she started in on Blair.  
>"That waiter thought you and Dan were a couple and you didn't correct him is there something you want to share with me. Your best friend. "<p>

"Seriously Serena that's what you dragged me in here for. Dan and I arrived together holding hands. He just assumed we were a couple there was no point on correcting him."

"Want to explain the holding hands part."

"Sure, Dan is one of my best friends I love him I grabbed his hand because I wanted to. Not because we're a secret couple. Now if you're done interrogating me I'm going back to the table." Blair yelled as she stormed off.

Meanwhile at the table.  
>"So Humphrey bet in high school you never would have thought one day you and Blair would get mistaken as a couple." laughed Nate.<p>

"No if you had told me that One day someone would mistake me and Blair as a couple I would have suggested you seek help but things change. It was an honest mistake I mean we came in together and we were holding hands."

"Yes son I never realized you were the hand holding type."

"OMG I just left this conversation from the girls yes me and Dan were holding hands okay what's the big deal." Snapped Blair who had just arrived back at the table.

Luckily just as the rest of the females got back to the table so did the entrees. The rest of lunched passed smoothly as it was spent with the boys inhaling the food. And the girls discussing were they should shop. Soon enough lunch was over. They group decided it would be easier to walk to the stores they wanted to go to. As most of them were only a street or two over.

When the stood over Blair grabbed Dan's hand and said they would lead the way while glaring daggers at everyone daring them to say something and dragged him off. 

"That was perfect Dan thy definitely think something's going on between us."

"Yeah so seeing a your meant to like me does that mean your jot going to torture me while were shopping."

"Don't be silly Dan it means I'm going to torture you even more."

"Well a guy can wish."

"I do it know because I love you Dan."

"That makes it do much better as long as you love me."

"You're going to smile Dan it's still going to be you. Just a better dressed version."

"Your luck you're cute. What's first on my list of torture."?

"Jeans you know the more agreeable you are the faster this will be over. We're here."

Blair dragged him over to the changing room an told him to sit on the seat wear minutes later he was joined buy the rest of the guys while the females of the group went clothes hunting the rest of the afternoon was spent going shop to shop, Dan trying on countless clothes. The schemers and parent watching Dan and Blair's interaction. Dan and Blair bringing the conversation back to the other.


End file.
